Help me understand John Coltrane .... seriously.

I’m still not a big fan of Bitches Brew,  but at the same time I get why historically it is such a famous landmark recording.  

Erik,

Might help to mention what jazz you DO like.

For a Trane newbie, I'd suggest Ascension.
I'm joking.
I'd try these in order:

Lush Life (Prestige)
Coltrane Plays The Blues (Atlantic)
My Favorite Things (Atlantic)
Bags And Trane (Atlantic)

"My Favorite Things" is an obvious influence on rock musicians, you can hear it in his solos on that track.

I've been exactly where you are.  Don't force it, let the music come to you.  

On the flipside, JC,  was never afraid to stretch out. This aspect of his genius can present a complexity in appreciation. Agreed, allow the music to come to you.

Happy Listening!

I suggest you try some Cecil Taylor.  Conquistador! is excellent.  Coltrane will suddenly seem very mainstream and accessible.

Jazz is a continuum in terms of styles and flavors and can be appreciated in different ways through our own collective experiences.  Everyone’s path is different.  I grew up hearing classical music and big band jazz, but didn’t really embrace it until later in life (now more so than my own parents).  It’s almost a cliche to say that my jazz collection officially started with Miles Davis’ “Kind of Blue”, but that is the case.  I started building my collection around those players:  Miles Davis, John Coltrane, Bill Evans, Cannonball Adderley (and Miles’ next great quintet:  Herbie Hancock, Wayne Shorter, Tony Williams, Ron Carter).  I didn’t appreciate fusion until much later.  I think Coltrane up through “Kind of Blue” is very accessible followed by works with his first quartet (Elvin Jones, Jimmy Garrison, McCoy Tyner) - particularly during his Atlantic years.  With the Impulse years you start to see him push the boundaries - post quartet can be a challenge for most and probably something you have to be in the mood for (just like anything).  Like with most music you have to work up to it and give it some time assuming you have some level of passion for the genre.  Some days I crave more melody in my cereal and other days more dissonance.  Enjoy the journey!